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Volumn 40, Issue 40, 1999, Pages 7261-7265

Vinylic C-F bond activation with low-valent zirconocene: The generation and cross-coupling reactions of 1-fluorovinylzirconocene

Author keywords

Coupling reactions; Fluorine; Fluorine compounds; Olefins; Zirconium; Zirconium compounds

Indexed keywords

ALKENE; DIMETHYLAMINE; FLUORINE; IODIDE; ORGANOFLUORINE DERIVATIVE; PALLADIUM; TRIFLUOROETHANOL; VINYL DERIVATIVE; ZIRCONIUM; ZIRCONIUM DERIVATIVE;

EID: 0033215508     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01491-4     Document Type: Article
Times cited : (59)

References (32)
  • 10
    • 0032496937 scopus 로고    scopus 로고
    • and references cited therein
    • Ito, H.; Kuroi, H.; Ding, H.; Taguchi, T. J. Am. Chem. Soc. 1998, 120, 6623-6624 and references cited therein. Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039-11040.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 6623-6624
    • Ito, H.1    Kuroi, H.2    Ding, H.3    Taguchi, T.4
  • 13
    • 0028226811 scopus 로고
    • For reviews on fluorinated vinylmetals, see: Burton, D. J.; Yang, Z.-Y.; Morken, P. A. Tetrahedron 1994, 50, 2993-3063. Normant, J. F. J. Organomet. Chem. 1990, 400, 19-34.
    • (1994) Tetrahedron , vol.50 , pp. 2993-3063
    • Burton, D.J.1    Yang, Z.-Y.2    Morken, P.A.3
  • 14
    • 0001915084 scopus 로고
    • For reviews on fluorinated vinylmetals, see: Burton, D. J.; Yang, Z.-Y.; Morken, P. A. Tetrahedron 1994, 50, 2993-3063. Normant, J. F. J. Organomet. Chem. 1990, 400, 19-34.
    • (1990) J. Organomet. Chem. , vol.400 , pp. 19-34
    • Normant, J.F.1
  • 15
    • 0030926481 scopus 로고    scopus 로고
    • and references cited therein
    • Most of α-monofluorovinylmetals reported so far incorporate either β-position bulky substituents or chelating functional groups, and/or use metals with highly covalent carbon-metal bond character such as Zn or Sn in order to enhance their thermal stability. Pelter, A.; Kvicala, J. Tetrahedron Lett. 1997, 38, 4877-4880 and references cited therein. Percy, J. M.; Wilkes, R. D. Tetrahedron 1997, 53, 14749-14762 and references cited therein. Chen, C.; Wilcoxen, K.; Zhu, Y.-F.; Kim, K.-i.; McCarthy, J. R. J. Org. Chem. 1999, 64, 3476-3482 and references cited therein. Kuroboshi, M.; Yamada, N.; Takebe, Y.; Hiyama, T. Tetrahedron Lett. 1995, 36, 6271-6274.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 4877-4880
    • Pelter, A.1    Kvicala, J.2
  • 16
    • 0030844926 scopus 로고    scopus 로고
    • and references cited therein
    • Most of α-monofluorovinylmetals reported so far incorporate either β-position bulky substituents or chelating functional groups, and/or use metals with highly covalent carbon-metal bond character such as Zn or Sn in order to enhance their thermal stability. Pelter, A.; Kvicala, J. Tetrahedron Lett. 1997, 38, 4877-4880 and references cited therein. Percy, J. M.; Wilkes, R. D. Tetrahedron 1997, 53, 14749-14762 and references cited therein. Chen, C.; Wilcoxen, K.; Zhu, Y.-F.; Kim, K.-i.; McCarthy, J. R. J. Org. Chem. 1999, 64, 3476-3482 and references cited therein. Kuroboshi, M.; Yamada, N.; Takebe, Y.; Hiyama, T. Tetrahedron Lett. 1995, 36, 6271-6274.
    • (1997) Tetrahedron , vol.53 , pp. 14749-14762
    • Percy, J.M.1    Wilkes, R.D.2
  • 17
    • 0032955440 scopus 로고    scopus 로고
    • and references cited therein
    • Most of α-monofluorovinylmetals reported so far incorporate either β-position bulky substituents or chelating functional groups, and/or use metals with highly covalent carbon-metal bond character such as Zn or Sn in order to enhance their thermal stability. Pelter, A.; Kvicala, J. Tetrahedron Lett. 1997, 38, 4877-4880 and references cited therein. Percy, J. M.; Wilkes, R. D. Tetrahedron 1997, 53, 14749-14762 and references cited therein. Chen, C.; Wilcoxen, K.; Zhu, Y.-F.; Kim, K.-i.; McCarthy, J. R. J. Org. Chem. 1999, 64, 3476-3482 and references cited therein. Kuroboshi, M.; Yamada, N.; Takebe, Y.; Hiyama, T. Tetrahedron Lett. 1995, 36, 6271-6274.
    • (1999) J. Org. Chem. , vol.64 , pp. 3476-3482
    • Chen, C.1    Wilcoxen, K.2    Zhu, Y.-F.3    Kim, K.-I.4    McCarthy, J.R.5
  • 18
    • 0029161698 scopus 로고
    • Most of α-monofluorovinylmetals reported so far incorporate either β-position bulky substituents or chelating functional groups, and/or use metals with highly covalent carbon-metal bond character such as Zn or Sn in order to enhance their thermal stability. Pelter, A.; Kvicala, J. Tetrahedron Lett. 1997, 38, 4877-4880 and references cited therein. Percy, J. M.; Wilkes, R. D. Tetrahedron 1997, 53, 14749-14762 and references cited therein. Chen, C.; Wilcoxen, K.; Zhu, Y.-F.; Kim, K.-i.; McCarthy, J. R. J. Org. Chem. 1999, 64, 3476-3482 and references cited therein. Kuroboshi, M.; Yamada, N.; Takebe, Y.; Hiyama, T. Tetrahedron Lett. 1995, 36, 6271-6274.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6271-6274
    • Kuroboshi, M.1    Yamada, N.2    Takebe, Y.3    Hiyama, T.4
  • 20
    • 0029655675 scopus 로고    scopus 로고
    • and references cited therein
    • Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291-304 and references cited therein. McCarthy, J. R.; Sunkara, P. S.; Matthews, D. P.; Bitonti, A. J.; Jarvi, E. T.; Sabol, J. F.; Resvick, R. J.; Huber, E. W.; Donk, W. A. v. d.; Yu, G.; Stubbe, J. In Biomedical frontiers of fluorine chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996; pp. 246-264. Bey, P.; McCarthy, J. R.; McDonald, I. A. In Selective fluorination in organic and bioorganic chemistry; Welch, J. T., Ed.; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991; pp. 105-133.
    • (1996) Tetrahedron , vol.52 , pp. 291-304
    • Welch, J.T.1    Lin, J.2
  • 21
    • 1842525830 scopus 로고    scopus 로고
    • Biomedical frontiers of fluorine chemistry
    • Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; American Chemical Society: Washington, DC
    • Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291-304 and references cited therein. McCarthy, J. R.; Sunkara, P. S.; Matthews, D. P.; Bitonti, A. J.; Jarvi, E. T.; Sabol, J. F.; Resvick, R. J.; Huber, E. W.; Donk, W. A. v. d.; Yu, G.; Stubbe, J. In Biomedical frontiers of fluorine chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996; pp. 246-264. Bey, P.; McCarthy, J. R.; McDonald, I. A. In Selective fluorination in organic and bioorganic chemistry; Welch, J. T., Ed.; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991; pp. 105-133.
    • (1996) ACS Symposium Series , vol.639 , pp. 246-264
    • McCarthy, J.R.1    Sunkara, P.S.2    Matthews, D.P.3    Bitonti, A.J.4    Jarvi, E.T.5    Sabol, J.F.6    Resvick, R.J.7    Huber, E.W.8    Donk, W.A.V.D.9    Yu, G.10    Stubbe, J.11
  • 22
    • 0002485698 scopus 로고
    • Selective fluorination in organic and bioorganic chemistry
    • Welch, J. T., Ed.; American Chemical Society: Washington, DC
    • Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291-304 and references cited therein. McCarthy, J. R.; Sunkara, P. S.; Matthews, D. P.; Bitonti, A. J.; Jarvi, E. T.; Sabol, J. F.; Resvick, R. J.; Huber, E. W.; Donk, W. A. v. d.; Yu, G.; Stubbe, J. In Biomedical frontiers of fluorine chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996; pp. 246-264. Bey, P.; McCarthy, J. R.; McDonald, I. A. In Selective fluorination in organic and bioorganic chemistry; Welch, J. T., Ed.; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991; pp. 105-133.
    • (1991) ACS Symposium Series , vol.456 , pp. 105-133
    • Bey, P.1    McCarthy, J.R.2    McDonald, I.A.3
  • 30
    • 0009705515 scopus 로고    scopus 로고
    • This zirconacyclopropanation/β-elimination protocol did not work on oxygen-free substrates such as 1,1-difluoroethylene, 2,2-difluorovinyldimethylphenylsilane, and tributyl(2,2-difluorovinyl)tin, presumably due to the difficulty in coordination of these olefins to the zirconocene complex
    • This zirconacyclopropanation/β-elimination protocol did not work on oxygen-free substrates such as 1,1-difluoroethylene, 2,2-difluorovinyldimethylphenylsilane, and tributyl(2,2-difluorovinyl)tin, presumably due to the difficulty in coordination of these olefins to the zirconocene complex.
  • 31
    • 0009680026 scopus 로고    scopus 로고
    • FH=20-23 Hz), which were in accordance with that of 5fe (20 Hz)
    • FH=20-23 Hz), which were in accordance with that of 5fe (20 Hz).
  • 32
    • 0009717075 scopus 로고    scopus 로고
    • note
    • +); found 271.1356.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.